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Chester Holiday Homes

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    Don't let other travellers get your favourite Chester area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 24 Rentals in Chester
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    Connecticut Retreat: a magical hide-away1 / 73
    (8)Excellent
    Chester
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Chester
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    The following rentals are within 15 kilometres of Chester.
    Old Lyme
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Old Lyme
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Washer
    • DVD Player
    • Air Conditioning
    • Patio
    • Waterfront
    • Ocean Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amazing remodel of this beachside, 4BR, 2Bath colonial. Two private beaches to choose from in this gated community. Dogs are welcome and a fenced area is provided! Plenty of room for 4 to 5 cars off street. The association includes access to basketball court, tennis courts, baseball diamond,...
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    Old Lyme, Connecticut 06371
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    9 ROOM WATERFRONT SUMMER COTTAGE (WITH 6 BEDROOMS) FOR RENT ON PRIVATE BEACH1 / 17
    (1)Average
    Clinton
    6 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • DVD Player
    • Waterfront
    • Satellite TV
    • Wi-Fi
    • Grill
    • Ocean Views
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **HEAVEN'S A LITTLE CLOSER IN A COTTAGE BY THE SEA** Weekly cottage for rent on PRIME SHORELINE location in CLINTON, CT. 9 ROOM, WATERFRONT Cottage, situated on a LARGE, PRIVATE BEACH only steps away from the ocean! Charm, Character, & Cleanliness! The cottage is professionally cleaned after each...
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    Clinton, Connecticut 06413
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 10
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    Stay at The Old Sindelar Farm1 / 17
    (5)Very good
    East Haddam
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Satellite TV
    • Washer
    • Hot Tub
    • Sauna
    • DVD Player
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 April 2017
    Picturesque, beautiful, and quiet! The house had everything that was needed for our group of girls, and the owners were wonderful and made us feel at home. Everything was clean...
    Reviewed 13 August 2016
    Doug & Doris are very friendly, they & their adult children work the small farm everyday. Doug greeted us and took my grandson on a tour to meet the calves, chickens and...
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    About this property
    Duplex house set on twelve rolling acres on The Old Sindelar Farm property. Many upgrades last year. House is fresh and clean. Enjoy the deck off the back for morning coffee or join us fireside at night. We have 3 beds, one queen with a memory foam mattress and two full size beds. All have 1800...
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    East Haddam, Connecticut 06423
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Old Saybrook
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A 2 Room, Small Cottage overlooking the Cornfield Point Private Beach on the Long Island Sound. INCLUDES: A fully stocked kitchen with microwave, coffeemaker, and toaster. A dinette table for four, A full-size custom futon sleeper sofa, a one half bath, with attached outdoor private hot and cold...
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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Old Saybrook
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A 3 bedroom, 1 1/2 bath home overlooking the Cornfield Point Private Beach on the Long Island Sound. FIRST FLOOR: A fully stocked kitchen with microwave and coffee maker. A dining area and formal dining room. A one half bath. A bedroom with two twin beds. Laundry Room also available. There is a...
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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Old Saybrook
    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    • Satellite TV
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **Charming** Genuine New England Large Ppty-Weddings-Reunions w/large garden This is a five bedroom with a working fireplace, The home sleeps 14 people. Since 2007, this historic and one-of-a-kind property, has been offered successfully for family reunions, retreats, weddings, film shootings,...
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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 14
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    Deep River
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Patio
    • Housekeeping Included
    • Satellite TV
    • Washer
    • Sauna
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Peace Barn is a cozy retreat close to art and culture and parks. You’ll love my place because of the outdoor space and the comfy beds. My place is good for families, couples, and furry friends. The Peace Barn sits on 15 acres of private land which can be used for group retreats, film making,...
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    Deep River, Connecticut 06417
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Clinton
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Parking
    • Ocean Views
    • Satellite TV
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private beach. Sleeps 10 people. Front of house has Long Island Sound Views and the back overlooks tranquil Marsh area. Large gourmet kitchen with Subzero refrigerator, two sinks, double wall oven, and microwave. Huge granite island for food prep and parties. Open concept living with kitchen...
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    Clinton, Connecticut 06413
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    East Haddam
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Sanctuary is a mind/body retreat and wellness center situated on a 40 acre, solar-powered land preserve with a walking labyrinth, permaculture gardens, beaver ponds, forest trails, an apiary, goats and chickens. We host yoga classes, meditation, sound healings, music, and various...
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    East Haddam, Connecticut 06423
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Old Saybrook
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Secure Parking
    • Grill
    • Patio
    • Satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Cottage was voted one of the top 10 unique places to stay in Ct, by Only in Ct. for 2016 The house features a private yard, perennial gardens, front sitting porch, hard wood floors, skylights, working fireplace and fire pit. The house is filled with colorful art, back splash in the kitchen is...
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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Old Lyme
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • Parking
    • Ocean Views
    • Satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I challenge you to find a cottage that provides more than our Pail and Shovel Inn at Old Colony Beach in Old Lyme, Connecticut! Known as - pail and shovel inn - all in one word online, we offer the following: Beds in 3 bedfrooms - King-size Bed (1) - Trundle (two twins) (2) - Twin/Single Bed...
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    Location Information
    Old Lyme, Connecticut 06371
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Westbrook
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • Wi-Fi
    • Patio
    • Housekeeping Included
    • DVD Player
    • Shared Garden
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rates Are Based on A 7 Night Minimum Stay for 2 Guests<BR> Located in the Quaint, Historic, Shoreline Town of Westbrook, CT Lies this Unique 2 Bedroom Cottage! Escape from It All ~ Walk to the Beach or Stroll Down to the Dock on the Property's Riverfront. The Cottage is 1/2 mile from Town Center...
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    Westbrook, Connecticut 06498
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Westbrook
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Ocean Views
    • Waterfront
    • Patio
    • Washer
    • DVD Player
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy our year round home, private beach, ample sleeping and luxurious finishings. Views ABOUND from ALL floors. Enjoy a loaded granite luxury, stainless steel kitchen with sweeping Sound views and breezes. Large living and dining area that easily seats 10 people. Beautifully furnished with...
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    Westbrook, Connecticut 06498
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Old Saybrook
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is located in a quiet, friendly beach neighborhood. In summer you have access to 2 private beaches on the LI Sound. Both are within blocks of the house and can be walked in about 5 minutes or driven in about 2 minutes. There is a marina, children's playground, gazebo and more. In the...
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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Old Saybrook
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct Ocean Front-walk down the stairs and you are on the beach!! Three (3) Bedrooms (1 Queen, 1 Full, 1 Twin) plus loft with twin bed and pull out sofa. Enclose porch facing ocean for eat-in dining. Spacious living room, full kitchen. Outdoor shower with heated water. Kayaks provided. Gas grill....
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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Save $500 off CT Lake Front  Victorian Mansion Truly Memorable1 / 21
    (3)Very good
    East Haddam
    7 Bedrooms, 4 Bathrooms, Sleeps 24 Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Grill
    • Waterfront
    • Washer
    • Wi-Fi
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideal Connecticut location on Beautiful Crystal Clear Bashan Lake. Victorian Mansion with magnificent water views. Perfect setting for family vacations, and family reunions!! Taking reservations thru Dec. 2018. Just 1 3/4 hours from New York or Newport RI or 2 hrs. from Boston! Canoe, kayak,...
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    East Haddam, Connecticut 06423
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 24
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    Haddam
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Mountain Views
    • Grill
    • DVD Player
    • Balcony
    • Parking
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the historic town of Haddam, Connecticut on five park-like acres surrounded by nature, The Carriage House is the perfect getaway for discriminating travelers. Newly constructed and completed in 2015, The Carriage House offers approximately 1,000 sq. ft. of luxurious living space....
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    Haddam, Connecticut 06438
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Laurel Cottage1 / 15
    (2)Excellent
    Haddam
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Satellite TV
    • Outdoor Dining Area
    • Parking
    • Patio
    • Air Conditioning
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This is a wonderful place to spend some time decompressing from your busy schedule. The location is on the grounds of a lovely BB, The Brainerd House in Haddam, CT. It us a a...
    Reviewed 21 August 2015
    We were delighted with EVERYTHING about the Laurel Cottage (on the property of the Nehemiah Brainerd House B&B in Haddam)!! From the moment we arrived, the owners Maryan...
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    About this property
    Secluded behind a stand of tall pines, the Laurel Cottage has been restored and expanded to include a full kitchen, bathroom with double pedestal bathtub and a large subway tiled shower. A cozy double brass bed in the Great Room and a luxurious pull out queen size bed on the all season porch...
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    Location Information
    Haddam, Connecticut 06438
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Westbrook
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Perfect Getaway! Walk to the Beach or Relax on the Patio overlooking the Properties Dock by the River! Close to Area Attractions such as Goodspeed Opera House, Gillette's Castle, Towns of Mystic, Essex and New Haven Near Vineyards, Mohegan Sun & Foxwoods Casinos, Antiquing, Parks, Museums, Art...
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    Location Information
    Westbrook, Connecticut 06498
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Old Saybrook
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A lovely 3 bedroom, 2 bath home on a private cul de sac is just steps away from a private beach. It sleeps 6 comfortably. The home is fully equipped with linens, towels and all kitchen necessities. There is air conditioning and wifi. A wonderful spot to relax at the CT Shore. It is a short drive to...
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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Steps Away from Private Beach1 / 19
    (1)Excellent
    Old Saybrook
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Satellite TV
    • Internet Access
    • Grill
    • Air Conditioning
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A newly renovated home at the end of a cul de sac which offers privacy in a quiet neighborhood. It is a lovely open concept house that has a large deck and patio with water views. There is a very large side yard perfect for family volleyball and baseball games. The kitchen is fully equipped. There...
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    Location Information
    Old Saybrook, Connecticut 06475
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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